The Most Hilarious Prom Moments Caught On Film

By Steve Becker, April 14, 2018

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Everybody remembers their high school prom. But for some people, the experience was extra memorable because of the rather hilarious photos they’ve left behind. In many ways, these photos aren’t just a way to remember your friends, your date, or the time you had at prom night, but they’re also a time capsule that reminds you of the often awful trends and styles that we have thankfully left far, far behind. Take a minute to bask in the hilarity of these crazy and unforgettable prom photos.

Staring At The Sun

We all know that teenagers are… excited, let’s say? They’re on the cusp of adulthood, a few months away from moving out of their parents home, and all of a sudden they’re thrown into the event where the girls are dressed like movie stars. The guys, typically, still act and look like awkward goobers. They’ve yet to learn many of life’s important lessons, one of which is DON’T STARE!

The Dark Side Of Prom

Look, youngsters. Everyone knows about the raging hormones that can become a big part of prom night. All of your teachers, parents, and chaperones have been young before, as hard as it may be to believe. But usually, you keep this sort of unbridled lust out of your official prom pictures and in the back seat of a crappy car, where it belongs. Come on, now.

Stop Staring!

Once again, a teenage boy cannot help but react like a child given a juice box on a hot day. Get it together, kid! This girl obviously thought you were cute enough to go to prom with, but she’ll probably regret it when she sees how immature you are.

Too Much Affection

Compared to the previous pictures, this couple actually seems to like each other. They’re smiling and look great together. What is a bit much is grabbing her behind. She likes it, he likes it, but is this really the Prom Picture they want to be remembered for? Public displays of affection are fine within limits, but they should make the people around you uncomfortable not embarrass you twenty years later when you’re sharing pictures with your kids.

Photo Bomb, Indeed

This is one of those rare photo bombs where the person in the background actually looks like they want to bomb something. The guy in the back is probably just bored with waiting while the girls take their 97,000th photo to get it juuuuuust right, but he needs to remember that if you’re in the picture-takers view, you may just end up providing the internet with one of the best photobombs ever.

Llama Have A Good Time Tonight

Farm girls are certainly proud of the fact that they can get their hands dirty with the best of them, but do you really need to take prom photos with your llama, for crying out loud? If you look closely, the blonde girl looks a lot more pleased than her date does in this pic. Maybe that’s because he’s been through this dozens of times as they’ve already gotten photos with her chickens, cows, horses…

Devilish

Wearing matching outfits is one thing. Going to Spencer’s in the mall, buying some corny fake demon horns and going as High School Satan and his little devilette to prom? That’s quite another thing entirely. Add in the greasy red and black face paint that will be dripping down that guy’s face once he starts sweating on the dance floor and you have a recipe for disaster.

Birds Of A Feather

At first glance, this is a pretty normal photo. None of these lovely young ladies are committing any fashion crimes or wearing any regrettable hairstyles. And yet, look a little further, and you’ll see that they’re all posing with chickens for some reason. Are these girls just avid farmers? Are those their dates? Are they not a bit concerned about one of the chickens getting too excited and clawing through their gowns or worse yet, vacating their bowels?

Jungle Mess

Somebody should have told the prom organizers that they didn’t have to put the year 1985 in the “Jungle Love” sign. Trust us, we can all tell that this photo is from the mid-80s. I mean, look at the hair, for crying out loud. You have to hand it to the guy for wearing such an elaborate suit, and with tails! He definitely brought a little more style to the occasion than his date, who’s rocking a polka-dot dress.

Leave The Past Behind

There are some trends that are definitely left back in the past, such as every single trend that’s going on in this photo. From the girl trying to channel Annie Lennox of the Eurythmics to the guy, who appears to be Lionel Richie rocking a strange skunky mullet and studded collar outside of his dress shirt, this is all just…bad. Very, very bad.

Smiling’s For Posers

Imagine being the guy on the left. You’re too cool to smile for a photo, but you’re not too cool to skip prom altogether. If you’re really counterculture, why are you dressing up and getting your photo taken? His girlfriend looks happy, although she may be headed off to see her grandmother in the woods instead of to the dance. The other two are just wondering how they got themselves into this strange foursome.

At A Prom Far, Far Away

Some people take their love of Star Wars really, really far. This couple would be among those folks. The girl has decided to wear the elaborate garb of Queen Amidala, and her date looks like a somehow even whinier Anakin Skywalker than Hayden Christensen played in the prequels. And isn’t it unfair? She had to wear that crazy headdress and all that makeup, and he just got to pick up a brown bathrobe and a toy lightsaber and voila! He was done.

Cover Up

We can only assume from the choice of hairstyles here that both of these fine young people are hiding some sort of disfigurement on the left side of their faces. Why else are they both using their hair to cover up half of their faces? Then again, they do look quite pale, so maybe they’re just trying to cover up as much skin as possible to avoid the inevitable sunburns?

His And Her Haircuts

These two obviously went to Supercuts for matching his and her haircuts before the prom. Maybe they had a two-for-one special and the savings helped them go to Sizzler that night. If it wasn’t for the fact that the guy is wearing a tux, you would have guessed that these were twin sisters that decided to go to the prom together without dates.

Red, White & Ew

Redheads tend to have pale skin, but why you’d choose to accentuate that by dressing head to toe in white as a couple is beyond me. Then again, the guy didn’t go entirely head to toe; he couldn’t resist wearing his black boots despite the fact that they don’t fit in with what he’s wearing at all. And don’t get me started on the matching perms and deer-in-the-headlights expressions.

New Wave

These two look like a new wave duo from the 80s. The guy with the lopsided hair plays the synthesizer and does backing vocals, while the girl with the hair three times the size of her head dances in place like Debbie Harry and sings in an extremely high voice. Well, that is, when they’re not turning heads by being the most clutch couple at the entire prom. Sure, make fun of them now, but you know they were probably the most popular couple in school.

A Happy Occasion?

At first glance, there’s nothing odd about this picture. But then you start to notice little things, like how the girl on the left is wearing a dress that is waaaaay too tight and that the girl on the right does not look happy to go to prom. Lighten up, ladies! This is supposed to be the best time of your life.

Life Could Be A Dream

“Hey, guys, I know we all look way studly tonight and all, but I’m worried that when we take a photo of the four of us as a group, we won’t look that cool. Like, we might even look kinda dorky. Wait, I know! Jake, make sure you wear your totally cool sunglasses for the photo. And you know what else? None of us should smile. Let’s just look completely serious at the camera like it’s a bad band photo. This is gonna be great!”

Big Age Difference

The 1980s are a veritable treasure trove for awkward prom photos, but this one makes me a little bit uncomfortable. Oh, I know why! Because the guy looks like a 35-year-old used car salesman and she looks barely out of middle school! I guess age of consent wasn’t a thing back then, or what? I’m surprised he was able to get the night off at the factory to take his 13-year-old girlfriend to the prom.

Anywhere But Here

The girl in this photo has a resigned look on her face as if she’s trying to make the best of an awkward situation, but her date definitely does not have that kind of resolve. He does not look happy at all. Sure, maybe she’s not your dream date, but you’re not exactly her Mr. Right either, you bargain basement Kevin Bacon, you. At least muster a smile and stay awake for the photo.

Lookin’ Groovy!

Ah, the 1970s. A time of peace, love, and plaid. You can tell these two were a good looking couple, despite his oversized bow-tie and her…corsage? It’s hard to tell. It looks more like she won second prize showing livestock at the county fair, but maybe that was a sign of the times. As for the mushroom and pinwheel decor? Your guess is as good as mine.

Caught In The Act

We need the backstory for this one. Was this court-admissable evidence in the form of a photo taken right after this dweeb ditched his date’s dead body in the bushes? Hopefully not. Let’s just assume that it’s a normal, although awkward, guy that has an overbearing mother that wanted at least one picture of “just him” before he finally escaped and got to go to the prom.

Just Go With It

Well, this prom participant certainly took the theme seriously. When she heard that it was a storybook castle-themed affair, she decided to go full Victorian with her dress. In all fairness, he certainly doesn’t seem to mind. Anyway, when you put it all together you get a photo that looks dated in a much different way than the others on this list. This photo looks like it’s from the ’80s, after all, but specifically the 1880s.

On Patrol

What in the wide, wide galaxy is going on in this prom photo? This guy looks like a clone trooper that wanted to take his girlfriend to prom, but couldn’t get the night off work from his commander. Is he working security against potential Sith attacks at prom or something? No? Oh, that’s right…he just thought it’d be super cool to wear a Star Wars helmet for prom photos. Sure, guy. Sure.

It’s A Deal!

You have to wonder what’s going on in this photo. They’re supposed to be holding hands in a romantic way here, but instead they appear to be sealing some sort of business deal with a handshake. And am I crazy, or does he look about ten years older than her? Maybe it’s just because of the way he’s blushing. Have you ever seen a more nervous looking prom photo?

Arriving In Style

Obviously, these two weren’t actually going to ride a snowmobile to prom, but it’s funny that this guy is so in love with riding his snowmobile that he thought posing for this photo somehow made any semblance of sense. “Hey, you know what’d be great? Let’s pose on my snowmobile with some fake snow before we head to the prom!” No, that’s not a good idea, Jerry. Not at all.

You Can’t See Me

I don’t think even WWE superstar John Cena would approve of this look, and it’s hard to think of someone who appreciates wearing shorts to any occasion more than him. Seriously, what was this guy thinking? From the waist up, they look like a perfectly normal couple. And then you look down and what do you see? Pasty white calves. Why oh why? To her credit, she seems to be taking it all in stride.

Superdorks

It’s hard to hate on these two couples too much, given how much fun that they seem to be having together. But come on, guys…it’s not Halloween, it’s prom! But again, the girls have great senses of humor about it and who knows…maybe they were wearing tuxes underneath their costumes and they took them off right after this photo? We can hope, anyway.

What A Gag!

These three are having a great time hamming it up and pretending like they’re going to jump in the pool with their prom dresses on. Ha. Ha. Sooooo funny. Besides the corny gag, you’ve got the matter of their dresses, which are unfortunate. The girl on the left looks like she’s dressed to impress at a funeral, while the girl on the right is doing her best Disney princess impersonation.

Mature For His Age

Oy vey. Earlier we had the 35-year-old used car salesman with his teenage girlfriend, and now we’re on to the 16-year-old boy who apparently asked his teacher to go to the prom with him. I’m sure this young lady would say that the boy with her is “mature for his age,” but I’m not sure that excuses what appears to be about a ten-year age gap.

The Look Of Intensity

It’s hard to say whether this girl’s date is a boy, girl, or AI-powered cyborg, but that is a very intense looking facial expression right there. Did the photographer say, “Hey, look at your date adoringly and have your date stare stone-faced right at the camera?” Was that the case or was it just their idea to do this on the spot? And is the cyborg wearing black motorcycle gloves?

She Likes “Bad Boys”

Oh, poor Jessica. She tells everyone that she’s into “bad boys” and then shows up at the prom with…this guy. I mean, he does have a tattoo, right? Well, if it’s real. And look! He’s got not one, but two studded belts on and a frosted perm piled up on top of his head. No one is gonna mess with this dude and his 12-inch pythons at the high school dance. If nothing else, she looks proud of her choice.

Did You Spot Him?

These two guys are feeling pretty good. Getting ready for the prom, looking pretty dapper in their suits, and posing for the last of the obligatory photos for Mom and Dad. Then, they see this photo a couple of days later and lo and behold, there’s a dude hiding in the bushes behind them photobombing! But I’m thinking these two had the last laugh because clearly, the friend wasn’t dressed for prom and was going to stay home while they had fun.

Guess The Decade

Well, you can take one look at this photo and guess the decade this prom took place in pretty easily. This is a great photo because you have every type of mullet here. The male and female versions of the perm mullet, the blue-collar spiked mullet, even the Kevin Bacon floppy bangs mullet! And everyone is taking themselves so seriously! Ahhh, the 80s. What a decade.

Grin And Bear It

Well, this guy is a good sport, isn’t he? Not only did his date’s mom and sister want to get a photo with them, but they suggested this, uh, awkward pose. And yet there he is, smiling and giving 110% because he’s got a good sense of humor. Or maybe he just wants to get this photo done right the first time so he can get far, far away.

Big Johnny Depp Fans?

I’m gonna go out on a limb right now and say that these two are probably big fans of the movie Edward Scissorhands. And the band The Cure. And probably every piece of film that Tim Burton has ever directed. These two may be a little artsy-fartsy, but they also look like a pretty happy couple, hair crimes aside. Let’s let them enjoy their moment, shall we?

Let Me See Your Grill

It’s hard to tell if this girl is smiling, grimacing in pain, or just posing for the cover of her new rap album. Yes, it’s no fun having braces. But let’s be honest here, your teenage years are awkward, anyway. So if you’re going to spend a couple of years with railroad tracks on your teeth, it may as well be when you’re also making questionable hair and wardrobe choices (as also seen here).

It’s Not Easy Being Green

I can’t be imagining this…this girl is about as far as she can possibly get away from her date while still being in the photo with him, right? That is not the face of a girl who’s happy to be at prom. She took all that time to pick out her green dress and matching shoes, only to realize that her date looks like an over-the-hill rocker who’s gained weight since his band’s glory days.

Gravity Defying

You may look at these two and want to immediately mock their hair, but I think it’s impressive that they actually made it to prom at all with all the time they had to spend getting their hair to stand straight up perfectly. What’s strange is that her date doesn’t seem to know where the camera is. Or is he looking at that strand of hair that’s falling down towards his nose? If only he used a bit more hair gel.

Sunny Daze

You have to feel for this poor girl. She wants to have a good time with her date on the most important night of the entire year (maybe her whole life so far) and her dress is being upstaged…by her hair. Seriously, where does her hair get off not only almost completely swallowing her face, but also taking up about 1/3 of this photo? Maybe all the sunlight that’s washing out this photo has also frizzed up her hair?

She’s Hooked

This young man certainly thinks he’s found quite a catch, but I’m thinking that dress may have looked better on a different date. There’s something to be said for having a sense of humor on prom night, but I doubt that showing up with a huge fake fish is the kind of thing that’s going to woo the ladies and make them want to cut in during that last slow dance.

To The Candy Shop

“Let’s coordinate our outfits,” she said. She told him she was wearing red and white and he said, “sure, I got you.” She thought he’d show up in a white suit, maybe a red jacket or cummerbund. But no, instead he showed up looking like a peppermint stick, or maybe a barbershop ole. And worse yet, he didn’t bother to shave that thing that’s growing on his upper lip. It’s certainly not a mustache!

Something In Common

These two definitely have something in common, but it’s nothing particularly romantic. It’s more about the fact that they both choose strangely oversized frames for their glasses. Aside from wearing an old man’s bifocals, they’re not dressed too poorly if you ignore the fact that she’s rocking a tablecloth that’s been cut into an outfit that you’d expect to see an old lady wear to church.

What A Mismatch

Given that the 80s were a strange decade, but even by those standards, these two seem like a mismatch. This guy looks like he was president of the computers club and borrowed his grandpa’s old suit from when he was a door-to-door salesman. Meanwhile, this girl looks like a party girl through and through, teased five-inch-high bangs and all. Hey, maybe they have more in common than we think?

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